Ammonia → HCID 69792683, compound

Participants

Reaction Steps

A solution of 1.27 g (2.43 mmol) of ethyl 3-{3-[3-(5-carboxypentyloxy)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl]-4-methoxyphenyl}acrylate obtained in Example 24(a) dissolved in 35 ml of dichloromethane was introduced into a round-bottomed flask, 505 μl (2.55 mmol) of dicyclohexylamine were added, and the mixture was stirred for 10 minutes. Then 186 μl (2.55 mmol) of thionyl chloride were added dropwise and the mixture was stirred at room temperature for 10 minutes. The reaction medium was evaporated to dryness, the residue obtained was taken up in ethyl ether, the suspension was filtered and the filtrate was evaporated. The residue obtained was dissolved in 15 ml of THF and the solution was introduced dropwise under nitrogen into a three-necked flask containing 20 ml of THF, 405 μl (2.92 mmol) of triethylamine and 160 μl of a 34% aqueous ammonia solution (2.67 mmol). The mixture was stirred at room temperature for 30 minutes, the reaction medium was poured into water, acidified to a pH of 1 with 1N hydrochloric acid and extracted with ethyl ether, and the organic phase was decanted, dried over magnesium sulfate, filtered and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of heptane and ethyl acetate (80:20). After evaporation of the solvents, 750 mg (60%) of the expected compound were obtained in the form of a white powder having a melting point of 133°-135° C.

Provenance & Evidence